38477-52-0Relevant academic research and scientific papers
Synthesis, characterization, and application of CoFe2O4@TRIS@sulfated boric acid nanocatalyst for the synthesis of 2-amino-3-cyanopyridine derivatives
Faroughi Niya, Homayoun,Hazeri, Nourallah,Maghsoodlou, Malek Taher,Fatahpour, Maryam
, p. 1315 - 1330 (2021/02/11)
Abstract: The aim of this research is the synthesis of a novel acidic nanocatalyst using the layer-by-layer assembly technique. The CoFe2O4@TRIS@sulfated boric acid nanoparticles were easily synthesized and studied as a highly beneficial, recyclable, and magnetite nanocatalyst for the synthesis of 2-amino-3-cyanopyridine derivatives. The chemical structure of CoFe2O4@TRIS @sulfated boric acid nanocatalyst was completely confirmed with different techniques like FESEM, Map, EDS, XRD, TGA/DTG, VSM, and FT-IR analyses. Briefly, the newly synthesized nanocatalyst offers some advantages such as simplicity of work-up, highly stable, environmental friendliness, reusability, excellent yields, and short reaction time. Graphic abstract: [Figure not available: see fulltext.].
Application of salicylic acid as an eco-friendly and efficient catalyst for the synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives
Roozifar, Majid,Hazeri, Nourallah,Faroughi Niya, Homayoun
, p. 1117 - 1129 (2021/02/26)
In this study, three eco-friendly, efficient, and convenient protocols have been reported for one-pot synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives using salicylic acid as a catalyst under solvent-free condition. The reported protocols offer several significant advantages such as the application of a nontoxic, neutral, and cheap catalyst, environmentally friendly conditions, the easy isolation of products by filtering, short reaction times, simple methodology, and good yields.
Amberlyst-15 catalysed sonochemical synthesis of 2-amino-4,6-disubstituted nicotinonitrile derivatives and their biological evaluation
Challa, Chandra Sekhar,Katari, Naresh Kumar,Nallanchakravarthula, Varadacharyulu,Nayakanti, Devanna,Kapavarapu, Ravikumar,Pal, Manojit
, (2021/06/07)
The 2-amino nicotinonitrile framework has been explored first time for the identification of potential inhibitors of SIRT1. Thus a series of targeted 2-amino-4,6-disubstituted nicotinonitrile derivatives were synthesized by employing an ultrasound assisted MCR of ketones, aldehydes, malononitrile and ammonium acetate. The MCR was carried out in the presence of Amberlyst-15 in MeCN under mild conditions to give the desired product in good yields. The reaction was less efficient in the absence of air whereas combination of Amberlyst-15, ultrasound, air and MeCN was essential for the success of this MCR. Several of the synthesized compounds showed good activities when tested for their SIRT1 inhibitory potential in vitro among which 5c, 5e and 5n were identified as the most potent (IC50 ~ 3 μM) and were better than the known inhibitor nicotinamide (IC50 ~109 μM). In the in silico docking studies these three compounds showed better binding energy (> 100 kcal/mol) and higher number of interactions than nicotinamide (binding energy -88.38 kcal/mol). While both amino (–NH2) and cyano (–CN) groups of nicotinonitrile derivatives formed H-bonds with the ASN346 and HIS363 residue respectively the nicotinamide showed similar interactions with ASP348 and ILE347 through its amide (–CONH2) moiety. Compound 5c, 5e and 5n has been identified as initial hits for further study.
One-pot synthesis of 2-amino-3-cyanopyridines and hexahydroquinolines using eggshell-based nano-magnetic solid acid catalyst via anomeric-based oxidation
Akbarpoor, Tahere,Khazaei, Ardeshir,Seyf, Jaber Yousefi,Sarmasti, Negin,Gilan, Maryam Mahmoudiani
, p. 1539 - 1554 (2019/12/11)
Abstract: In the present research, the eggshell as a hazardous waste by European Union regulations was converted to a valuable catalyst, namely nano-Fe3O4@(HSO4)2. The as-prepared catalyst, first, was characterized using different techniques, including Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX), field emission scanning electron microscopy (FESEM), and transmission electron microscopy (TEM). Back-titration method confirmed the loading of a high surface density of acidic group, namely 8.8?mmol HSO4 per gram of the catalyst. The catalytic property of the as-prepared catalyst was examined in the synthesis of 2-amino-3-cyanopyridines via anomeric-based oxidation (ABO), and hexahydroquinolines derivatives. High yield, short reaction time, solvent-free condition, waste to wealth, and optimization with the design of experiment are the major advantages of the present work. Taken together, these results suggest the conversion of waste to wealth products around the world and usage in organic transformation. Graphic abstract: [Figure not available: see fulltext.].
Catalyst-free three-component synthesis of 2-amino-4,6-diarylpyridine-3-carbonitriles under solvent-free conditions
Sayahi, Mohammad Hosein,Saghanezhad, Seyyed Jafar,Mahdavi, Mohammad
, p. 725 - 728 (2019/08/28)
[Figure not available: see fulltext.] A novel efficient one-pot synthesis of 2-amino-4,6-diarylpyridine-3-carbonitriles is described. Method involves heating the mixture of an acetophenone oxime, aldehyde, and malononitrile without any catalyst under solvent-free conditions to give the title compounds in good to high yields.
The green synthesis of 2-amino-3-cyanopyridines using SrFe12O19 magnetic nanoparticles as efficient catalyst and their application in complexation with Hg2+ ions
kheilkordi, Zohreh,Mohammadi Ziarani, Ghodsi,Bahar, Shahriyar,Badiei, Alireza
, p. 365 - 372 (2019/01/28)
Abstract: In this paper, a family of 2-amino-4,6-diphenylnicotinonitriles are prepared from aromatic aldehydes, acetophenone derivatives, malononitrile, and ammonium acetate via one-pot reaction catalyzed by SrFe12O19 magnetic nanoparticles. SrFe12O19 was an efficient, green, and reusable nanomagnetic heterogeneous catalyst with the average particles’ size of 70?nm which can be recycled and readily and separated from the reaction mixture using an external magnet. Short reaction times and high yields of desired products are the main advantages of the presented procedure. Subsequently, the spectrophotometric method was used to investigation of the complexation process between 2-amino-4,6-diphenylnicotinonitrile as organo-ligand and several metal ions such as Ag+, Cd2+, Co2+, Cr3+, Cu2+, Fe3+, Hg2+, Mn2+, Ni2+, Pb2+, and Zn2+ in CH3CN solution at 25?°C. According to the obtained results, the absorption spectra of organo-ligand in the CH3CN solution only were changed by the addition of Hg2+ ions, which indicates the formation of one absorbing complex compound between organo-ligand and Hg2+ ions. The stoichiometry of the resulting complex was calculated from the computer fitting of the molar absorbance measurements in different mole ratios. Graphical abstract: [Figure not available: see fulltext.].
Fe3O4@TiO2@O2PO2(CH2)NHSO3H as a novel nanomagnetic catalyst: Application to the preparation of 2-amino-4,6-diphenylnicotinonitriles via anomeric-based oxidation
Zolfigol, Mohammad Ali,Yarie, Meysam
, (2017/04/21)
A new, green and reusable nanomagnetic heterogeneous catalyst, namely Fe3O4@TiO2@O2PO2(CH2)NHSO3H, was synthesized and fully characterized using suitable techniques such as infrared spectroscopy, X-ray diffraction, scanning and transmission electron microscopies, thermogravimetry, vibrating sample magnetometry and energy-dispersive X-ray spectroscopy. The applicability of the constructed heterogeneous core–shell catalyst as a promoter was successfully explored for the synthesis of 2-amino-4,6-diphenylnicotinonitrile derivatives upon the reaction of a good range of aromatic aldehydes, acetophenone derivatives, malononitrile and ammonium acetate. The desired products were obtained with good to high yields in short reaction times under solvent-free conditions. The suggested mechanism offers an anomeric-based oxidation route to the products in the final step of the synthetic pathway.
Graphene oxide: A reusable and metal-free carbocatalyst for the one-pot synthesis of 2-amino-3-cyanopyridines in water
Khalili, Dariush
, p. 1721 - 1723 (2016/04/04)
A one-pot synthesis of 2-amino-3-cyanopyridine derivatives has been demonstrated through the multicomponent reaction of aldehydes, ketones, malononitrile, and ammonium acetate using graphene oxide as a heterogeneous catalyst in water as a green medium. The graphene oxide catalyst is very mild, effective, and most of its activity is preserved after being reused for five times.
Urease-catalyzed synthesis of aminocyanopyridines from urea under fully green conditions
Tamaddon, Fatemeh,Ghazi, Somayeh,Noorbala, Mohammad Reza
, p. 89 - 92 (2016/04/05)
This is an original work on catalytic performance of urease in organic synthesis which in one-pot dissociation of urea and condensation of the in situ generated ammonia with aldehydes, acetophenones, and malononitrile occurs in water to give 2-amino-3-cyanopyridines. Comparative experiments with ammonium salts supported the enzymatic specify of 0.01 g/mL (50 U/mg) of urease for bio-production of ammonia, while trace amount of heavy metal ions such as Pb2+, Hg2+, and Ag+ inhibit these specific reactions. The scalability and promiscuity of urease facilitate the applicability of the process for biotechnological organic reactions based on ammonia.
A multicomponent synthesis of 2-amino-3-cyanopyridine derivatives catalyzed by heterogeneous and recyclable copper nanoparticles on charcoal
Khalifeh, Reza,Ghamari, Mahdiyeh
, p. 759 - 768 (2016/04/20)
An efficient and convenient method was developed for synthesis of 2-amino-3-cyanopyridine derivatives via the four-component coupling reaction between ketone, aldehyde, malononitrile, and ammonium acetate in the presence of 2 molpercent copper nanoparticles on charcoal (Cu/C) catalyst. A variety of ketones and aldehydes was used to afford the corresponding products in good to excellent yields. The method is applicable to large-scale operation without any problem. The catalyst could be quantitatively recovered from the reaction mixture by simple filtration and reused at least eight times with almost consistent activity.
